Azo dyestuffs from aminodiphenylenoxide



Patented Apr. 19, 1927.

UNITED STATES EUGEN GLIETENBERG, OF LEVERKUSEN, GERMANY, ASSIGNOR STUFF CORPORATION, OF NEW YORK, N. Y., A

PATENT OFFICE.'

T GRASSELLI DYE- CORPORATION OF DELAWARE.

AZO DYESTUFFS FROM AMINODIPHENYLENOXIDE.

No Drawing. Application filed December 2, 1925, Serial No. 72,814, and in Germany December 11,

I have found that the azo dyestufl's which i are obtained by coupling diazotized aminodiphenylenoxide of the formula v NH:

Amongst the arylids being particularly suited for my invention I might mention the alpha and beta-naphthalid, the chlortoluidlds, the anisidid and their chlorsubstitution products. When produced in substance my new dyestuffs are dark powders, substantially in- 3 soluble in water. By reduction as with zinc and hydrochloric acid theyv yield an aminodiphenylenoxide compound and an amino-2-3-hydroxynaphthoic acid compound. 7 In order to produce my novel compounds on the fibre the latter is usually first impregnated with an alkaline solution of the naphthoic-arylid, and the diazo solution either printed upon the cotton cloth or the fibre passed through a bath containing the diazo compound.

The iollowing example will further ilproximately through arylid a My novel products are particularly distinguished by clear claret shades and when produced directly on the fibre, by a very superior fastness to light and kier boiling.

They are obtained by diazotizing an aminodiphenylenoxide, a diaminodiphenylenoxid or other substitution products of aminodiphenylenoxide and coupling with a 2-3- hydroxynaphthoic acid arylid. The following structural formula represents an example of a dyestulf obtainable from a diaminodiphenylenoxid mentioned.

A cotton hank which has been impregnated with an alkaline solution containing ap- 20 grams 2-3-hydroxynaph thoic acid-anaphthylid per litre is passed a bath containing diazotized aminodiphenylenoxide of the formula and excess sodium acetate. The cotton is dyed an intense and clear Bordeaux of ex-. cellent fastness to washing, chlorine and kier boiling. s

I claim: 1. As new products azo dyestuffs of the general formula CO-NH which is a deep red powder, practically insoluble in water and yielding on reduction aminodiphenylenoxide and an amino-2-3-hydrogynaphthoicg acid-alpha-naphthalid.

3. As new products vegetable fibres dyed deep Bordeaux red shades, exceedingly fast to kier boiling with azo .dyestufl's of the general formula CO-NH-R in which R is an aryl radicle and'R the radicle of a diphenylenoxid compound.

4. As new products vegetable fibres dyed deep Bordeaux red shades exceedingly fast to chlorine, Washing and lrier boiling, witn Y .azo dyestuffs of the probable formula ore CO-NH In testimony whereof I have hereunto set I my hand.

EUGEN GLIETENBERG. 

